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Synthesis of [3.3.1] Bicyclic Compounds by a Brønsted Acid Catalysed Double Intramolecular Michael Addition
Author(s) -
Mendoza Abraham,
Pardo Pilar,
Rodríguez Félix,
Fañanás Francisco J.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001109
Subject(s) - bicyclic molecule , intramolecular force , michael reaction , brønsted–lowry acid–base theory , chemistry , intramolecular reaction , stereochemistry , catalysis , organic chemistry , medicinal chemistry
Cyclisation sequence : An efficient method for the synthesis of [3.3.1] bicyclic compounds from easily available ynone derivatives has been developed. The reaction is based on an unprecedented double intramolecular Michael addition (DIMA) of an oxygen‐centred and a carbon‐centred nucleophile to the ynone (see scheme).